View 208 Central Drive Chestertown, MD MLS# MDQA2016836
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$299,000
3

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1.0

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1,120

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208 Central Drive

Chestertown, MD

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View 126 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016812
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$349,000
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2.0

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1,304

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126 Char Nor Manor Boulevard

Chestertown, MD

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View 240 Merganser Drive Chestertown, MD MLS# MDQA2016900
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    $425,000
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    2.0

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    1,120

    Sq.Ft.

    240 Merganser Drive

    Chestertown, MD

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    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 2032 Pondtown Road Chestertown, MD MLS# MDQA2016688
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    $325,000
    3

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    2.0

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    1,120

    Sq.Ft.

    2032 Pondtown Road

    Chestertown, MD

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    Courtesy of NORTHROP REALTY
    View 136 Hilltop Drive Chestertown, MD MLS# MDQA2016782
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    $366,000
    3

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    2.0

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    1,432

    Sq.Ft.

    136 Hilltop Drive

    Chestertown, MD

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    View 107 Longfellow Drive Chestertown, MD MLS# MDQA2016720
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    $295,000
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    107 Longfellow Drive

    Chestertown, MD

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    View 720 Deep Landing Road Chestertown, MD MLS# MDQA2016758
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      $369,999
      3

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      2.0

      Baths

      1,271

      Sq.Ft.

      720 Deep Landing Road

      Chestertown, MD

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      View 704 Truslow Road Chestertown, MD MLS# MDQA2016632
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      $440,000
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      2.1

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      2,060

      Sq.Ft.

      704 Truslow Road

      Chestertown, MD

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      View 101 Coleman Drive Chestertown, MD MLS# MDQA2016624
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        OPEN HOUSE: Sunday 5/3 12:00 PM - 2:00 PM
        $524,900
        3

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        2.1

        Baths

        2,268

        Sq.Ft.

        101 Coleman Drive

        Chestertown, MD

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        View 205 River Road Chestertown, MD MLS# MDQA2016560
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        OPEN HOUSE: Saturday 5/2 12:00 PM - 2:00 PM
        $949,000
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        2.1

        Baths

        2,877

        Sq.Ft.

        205 River Road

        Chestertown, MD

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        View 0 Round Top Road Chestertown, MD MLS# MDQA2016578
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          $200,000
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          0.0

          Baths

          0 Round Top Road

          Chestertown, MD

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          View 206 Burchard Sawmill Road Chestertown, MD MLS# MDQA2016510
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            $29,000
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            0.0

            Baths

            206 Burchard Sawmill Road

            Chestertown, MD

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            View 113 Pear Tree Point Road Chestertown, MD MLS# MDQA2016478
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              $250,000
              3

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              1.0

              Baths

              1,296

              Sq.Ft.

              113 Pear Tree Point Road

              Chestertown, MD

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              View 109 Wilton Road Chestertown, MD MLS# MDQA2016312
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              $344,900
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              2.0

              Baths

              1,392

              Sq.Ft.

              109 Wilton Road

              Chestertown, MD

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              View 154 Longfellow Drive Chestertown, MD MLS# MDQA2016250
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                $299,000
                3

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                1.0

                Baths

                1,408

                Sq.Ft.

                154 Longfellow Drive

                Chestertown, MD

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                View 101 Pine Tree Road Chestertown, MD MLS# MDQA2016188
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                  $480,000
                  4

                  Beds

                  2.0

                  Baths

                  1,848

                  Sq.Ft.

                  101 Pine Tree Road

                  Chestertown, MD

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                  View 204 Double Creek Road Chestertown, MD MLS# MDQA2015996
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                  $598,000
                  3

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                  2.1

                  Baths

                  2,927

                  Sq.Ft.

                  204 Double Creek Road

                  Chestertown, MD

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                  View East Street Chestertown, MD MLS# MDQA2015588
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                    1 of 8
                    $88,900
                    Studio

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                    0.0

                    Baths

                    East Street

                    Chestertown, MD

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                    View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
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                      1 of 26
                      $185,000
                      3

                      Beds

                      2.0

                      Baths

                      1,666

                      Sq.Ft.

                      127 Wood Duck Lane

                      Chestertown, MD

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                      View 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
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                        $320,000
                        3

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                        1.1

                        Baths

                        1,096

                        Sq.Ft.

                        222 Dutchess Road

                        Chestertown, MD

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                        Courtesy of GUNTHER-MCCLARY REAL ESTATE

                        About Chestertown

                        Listings in Chestertown, MD

                        21

                        Estimated median home price

                        $325,000
                        Chestertown MD Homes for Sale & Properties

                        Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

                        Homes for Sale by Price in Chestertown, MD

                        PriceCount
                        $0 - 100K3
                        $100K - 200K2
                        $200K - 300K4
                        $300K - 400K6
                        $400K - 500K3
                        $500K - 600K2
                        $600K - 700K0
                        $700K - 800K0
                        $800K - 900K0
                        $900K - 1M1
                        $1M - Max0

                        Homes for Sale by Type in Chestertown, MD

                        Property TypeCount
                        Single Family17
                        Townhouse0
                        Condo0
                        Commercial0
                        Rental2
                        Lots and Land4
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 4/30/2026)

                        Find Properties in Chestertown, MD

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                        Information deemed reliable but not guaranteed.

                        Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

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